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Chapter 10: Problem 110

Sinmilarly, thiols are stronger acids than alcohols. Compare, for example, the p \(K\). values of ethanol and ethanethiol in dilute aquecous solution.

Short Answer

Expert verified
Answer: Thiols are stronger acids than alcohols because their conjugate bases are more stable due to the larger size and lower electronegativity of the sulfur atom compared to the oxygen atom in alcohols. This allows the sulfur atom to better stabilize the negative charge on the conjugate base, making thiols more inclined to lose a proton and thus more acidic.

Step by step solution

01

1. Write the chemical structures of ethanol and ethanethiol

To compare the acidity of ethanol and ethanethiol, we need to write their chemical structures. Ethanol (CH3CH2OH) is an alcohol, while ethanethiol (CH3CH2SH) is a thiol.
02

2. Look up the pKa values of ethanol and ethanethiol

To further compare their acidity, we need to look at their pKa values. The pKa value refers to the acidity constant - the lower the pKa value, the stronger the acid. The pKa value of ethanol is around 15.9, while that of ethanethiol is around 10.6.
03

3. Determine which compound is a stronger acid based on the pKa values

Comparing the pKa values, we can conclude that ethanethiol (pKa 10.6) is a stronger acid than ethanol (pKa 15.9) since its pKa value is lower.
04

4. Discuss factors contributing to the difference in acidity

One of the main factors that contribute to the difference in acidity is the stability of the conjugate bases formed after the loss of a hydrogen ion (proton). When ethanol loses a proton, it forms an ethoxide ion (CH3CH2O-), while ethanethiol forms an ethanethiolate ion (CH3CH2S-) when it loses a proton. The stability of the conjugate base is related to the electronegativity and the size of the atom attached to the hydrogen ion. Sulfur in ethanethiol is less electronegative (2.58) and larger in size compared to the oxygen in ethanol (3.44). These factors make the sulfur atom better able to stabilize the negative charge on the conjugate base, making it more stable than the ethoxide ion. Consequently, ethanethiol is more inclined to lose a proton, making it a stronger acid than ethanol.

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Most popular questions from this chapter

Write equations for the reaction of I-hatanol with each reagent. Where you predict no reaction, write \(N R\). (a) Na metal (b) \(\mathrm{HBr}\), heat (c) HI, heat (d) \(\mathrm{PBr}_{\mathrm{a}}\) (e) \(\mathrm{SOCl}_{2}\), proridine (f) \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{2}, \mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{H}_{2} \mathrm{O}\), heat (g) \(\mathrm{HIO}_{4}\) (h) PCC (i) \(\mathrm{CH}_{4} \mathrm{SO} \mathrm{C}\), pyridine

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